680624-39-9Relevant academic research and scientific papers
A new synthesis of α-fluorovinylsulfones utilizing the Peterson olefination methodology
Asakura, Noriaki,Usuki, Yoshinosuke,Iio, Hideo
, p. 81 - 88 (2003)
α-Fluoro-α-silyl-substituted sulfones 1 are readily prepared from fluoromethyl phenyl sulfone and the appropriate silyl chloride. The use of TBSCl improves both the stability and yield of 1. Lithium derivatives 4 undergo a smooth Peterson olefination reaction with less-enolizable carbonyl compounds to give moderate to good yields of the expected α-fluorovinylsulfones 6, in some cases with high E-stereoselectivity. One-pot reaction with 4 generated in situ from fluoromethyl phenyl sulfone in tetrahydrofuran (THF) also proceeds smoothly, particularly with aldehydes.
